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913472

Sigma-Aldrich

(2S,2S′,3S,3S′)-WingPhos

≥95%

Synonym(s):

(2S,2′S,3S,3′S)-4,4′-Di(anthracen-9-yl)-3,3′-di-tert-butyl-2,2′,3,3′-tetrahydro-2,2′-bibenzo[d][1,3]oxaphosphole

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About This Item

Empirical Formula (Hill Notation):
C50H44O2P2
CAS Number:
1435940-19-4
Molecular Weight:
738.83
UNSPSC Code:
12352200

Assay

≥95%

form

powder or crystals

optical purity

ee: ≥99% (HPLC)

reaction suitability

reagent type: ligand

functional group

phosphine

Application

(2S,2S′,3S,3S′)-WingPhos is a P-chiral biphosphorus ligand for Rh-catalyzed asymmetric hydrogenations as well as Rh-catalyzed asymmetric addition of aryl boroxines to ketones.

Product can be used with our benchtop hydrogen generator, H-Genie Lite (Z744083)

Other Notes

Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to N-Unprotected Ketimines: Efficient Synthesis of Cipargamin

Legal Information

Sold in collaboration with Zejun Pharmaceuticals

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Design of phosphorus ligands with deep chiral pockets: practical synthesis of chiral β-arylamines by asymmetric hydrogenation.
Guodu Liu et al.
Angewandte Chemie (International ed. in English), 52(15), 4235-4238 (2013-03-16)
Linwei Huang et al.
Angewandte Chemie (International ed. in English), 55(14), 4527-4531 (2016-03-05)
Highly enantioselective additions of arylboroxines to simple aryl ketones have been achieved for the first time with a Rh/(R,R,R,R)-WingPhos catalyst, thus providing a range of chiral diaryl alkyl carbinols with excellent ee values and yields. (R,R,R,R)-WingPhos has been proven to be
Jinbin Zhu et al.
Angewandte Chemie (International ed. in English), 58(45), 16119-16123 (2019-08-31)
Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with

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